Bismuth-Mediated Organic Reactions

Name: Bismuth-Mediated Organic Reactions
Brand: Springer
Price: 341.33 EUR
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Thierry Ollevier(Herausgeber*in)

Springer (Verlag)

Erschienen am 10. Januar 2012

XIV, 278 Seiten

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978-3-642-27239-4 (ISBN)

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Inhalt

Intro
Bismuth-Mediated Organic Reactions
Topics in Current Chemistry Also Available Electronically
Aims and Scope
Foreword
Preface
Bismuth in synthesis: an emerging area
Contents
Bismuth Catalysts in Aqueous Media
1 Introduction: Water-Compatible Lewis Acids
2 Chiral Bi(OTf)3-Catalyzed Asymmetric Hydroxymethylation in Aqueous Media
3 Chiral Bi(OTf)3-Catalyzed Asymmetric Ring-Opening Reactions of meso-Epoxides
4 Bi(OH)3-Catalyzed Allenylation
5 Conclusion and Perspective
References
Pentavalent Organobismuth Reagents in Organic Synthesis: Alkylation, Alcohol Oxidation and Cationic Photopolymerization
1 Introduction
2 Synthesis of Organobismuth(V) Reagents
3 Carbon-Carbon Bond Forming Reactions
3.1 C-C Bond Forming Reactions with Alkylbismuthonium Salts
3.2 C-C Bond Forming Reactions with Bismuth Ylides
4 Carbon-Heteroatom Bond Forming Reactions
5 Oxidation of Alcohols to Carbonyl Compounds
5.1 Oxidation with Triarylbismuth(V) Compounds
5.2 Oxidation with Tetraarylbismuth(V) Compounds
6 Photoinduced Cationic Polymerization of Oxiranes
7 Summary and Overview
References
Environmentally Friendly Organic Synthesis Using Bismuth(III) Compounds
1 Introduction
2 Synthesis of Acylals
3 Synthesis of Heterocycles Using Bismuth(III) Compounds as Catalysts
3.1 Bismuth Triflate-Catalyzed Synthesis of Substituted 3,4-Dihydro-2H-1-Benzopyrans
3.2 Bismuth(III) Bromide-Catalyzed Synthesis of Substituted Tetrahydroquinoline Derivatives
4 Cyclization Reactions Using Bismuth(III) Triflate as a Catalyst
4.1 Bismuth(III) Triflate-Catalyzed Carbonyl Ene Reactions
4.2 Bismuth(III) Triflate-Catalyzed Olefin-Epoxide Cyclizations
5 Bismuth(III) Iodide-Catalyzed Deprotection of Acetals
6 Bismuth(III) Triflate-Catalyzed Synthesis of Dioxolanes, Dioxanes, and Dioxepines
7 Bismuth(III) Salt-Catalyzed Allylations
7.1 Synthesis and Allylation of Acyclic Acetals
7.2 Allylation of Cyclic Acetals
7.3 Allylation of Dithianes
7.4 Allylation of Tetrahydropyranyl and Tetrahydrofuranyl Ethers
References
Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines
1 Bismuth-Catalyzed Addition to N-Alkoxycarbonylamino Sulfones
1.1 Introduction
1.2 Bismuth Triflate-Catalyzed Sakurai Allylation Reaction
1.3 Bismuth Triflate-Catalyzed Mannich-Type Reaction
2 Bismuth-Mediated Three-Component Addition Reaction
2.1 Bismuth-Mediated Three-Component Aza-Sakurai Reaction
2.2 Bismuth-Mediated Three-Component Mannich-Type Reaction
3 Bismuth-Catalyzed Mukaiyama Aldol Reaction
3.1 Bismuth-Catalyzed Mukaiyama Aldol Reaction of Silyloxyfurans
3.2 Bismuth-Catalyzed Mukaiyama Aldol Reaction of Dioxinone-Derived Silyl Dienol Ethers
4 Conclusions
References
Bismuth Salts in Catalytic Alkylation Reactions
1 Introduction
2 Bismuth(III) Salts for SN1-type Substitutions of Activated Alcohols
2.1 The Search for Environmentally Benign Friedel-Crafts Alkylations
2.2 Bi(OTf)3-Catalyzed Alkylations of 1,3-Diketones
2.3 Bi(OTf)3-Catalyzed Synthesis of Warfarin Derivatives
2.4 Bismuth(III)-Catalyzed Substitutions of Propargyl Alcohols
2.5 Diastereoselective Substitutions of Activated Alcohols
3 Bismuth(III)-Mediated Activation of Alkenes and Alkynes
3.1 An Efficient Hydroarylation Approach to 1,1-Diarylalkanes
3.2 Bi(OTf)3-Catalyzed Alkylation of 2,4-Pentanediones with Activated Alkenes
3.3 From Alkenes to Alkynes: Bismuth-Catalyzed Carbo-oxycarbonylations
4 Conclusion
References
New Applications for Bismuth(III) Salts in Organic Synthesis: From Bulk Chemicals to Steroid and Terpene Chemistry
1 Introduction
2 Preparation of Bismuth(III) Triflate and Analogues
3 Electrophilic Additions
3.1 Acylation and Related Reactions
3.1.1 Acylation Reactions
3.1.2 Fries Rearrangement
3.2 Sulfonylation Reactions
3.3 Chloro Sulfinylation Reaction
4 Cyclization Reactions
4.1 Diels-Alder Reactions
4.2 Hetero-Diels-Alder Reactions
4.2.1 Carbonyl-Diels-Alder Reactions
4.2.2 Aza-Diels-Alder Reactions
5 Bismuth(III) Reagents in Steroid and Terpene Chemistry
5.1 Oxidation Reactions
5.2 Nucleophilic Ring-Opening of Epoxides
5.2.1 Ritter Reaction of Epoxides
5.2.2 Ring Opening of Epoxides with BI(III) Salts
5.3 Rearrangement Reactions
5.3.1 Westphalen and ``Backbone´´ Rearrangements
5.3.2 Wagner-Meerwein Rearrangements
5.4 Cleavage of the C17-Dihydroxyacetone Side Chain of Corticosteroids
6 Conclusions
References
Cationic Bismuth-Catalyzed Hydroamination and Direct Substitution of the Hydroxy Group in Alcohols with Amides
1 Introduction
2 Bismuth-Catalyzed Intermolecular Hydroamination
2.1 Intermolecular Hydroamination of 1,3-Dienes
2.2 Mechanistic Studies
2.3 Intermolecular Hydroamination of Vinyl Arenes
3 Direct Substitution of the Hydroxy Group in Alcohols with Amides
4 Conclusion
References
Transition-Metal Catalyzed C-C Bond Formation Using Organobismuth Compounds
1 Introduction
2 Transition-Metal Catalyzed C-C Bond Forming Reactions
2.1 Heck-Type Arylation Reaction
2.2 Copper-Catalyzed C-C Bond Forming Reactions
2.3 Ligand Coupling Reaction of Organobismuth(III) and (V) Compounds
2.4 Reaction with Organoheteroatom Compounds
2.5 Reaction with Organic Halides and Triflates
2.5.1 Reaction with Acyl Chlorides
2.5.2 Reaction with Aryl Halides and Triflates
2.5.3 Reaction with Alkenyl Halides and Triflates
2.5.4 Reaction Mechanism
2.6 Carbonylative Reaction
2.7 Allylic Coupling Reactions
2.8 1,4-Addition Reaction of a,beta-Unsaturated Carbonyl Compounds
2.9 Other C-C Bond Forming Reactions
3 Conclusions
References
Bismuth(III) Salts as Synthetic Tools in Organic Transformations
1 Introduction
2 Reactions of Aziridines and Epoxides
2.1 Cross-Cyclization of Epoxides with Homoallylic Alcohols
2.2 Aza-Prins Cyclization of Epoxides with Homoallylic Amines
2.3 Allylation of Epoxides and Aziridines
2.4 Hydrolysis of Epoxides and Aziridines
2.5 Thiolysis of Aziridines
3 Addition and Condensation Reactions
3.1 Conjugate Addition of Indole to p-Quinone
3.2 Condensation of Isatin with Indole and Pyrrole
3.3 Condensation of 2,2-Dimethoxypropane with an Aromatic Amine
4 Cycloaddition Reactions
4.1 Aza-Diels-Alder Reactions
4.2 Intramolecular Hetero-Diels-Alder Reactions
5 Synthesis of Heterocyclic Systems
5.1 Synthesis of Tetrahydropyran Derivatives
5.1.1 Synthesis of 4-Amidotetrahydropyran Derivatives
5.1.2 Synthesis of 4-Tetrahydropyranol Derivatives
5.1.3 Synthesis of 4-Chlorotetrahydropyran Derivatives
5.2 Synthesis of Benzopyran Derivatives
5.3 Synthesis of cis-Aziridine Carboxylates
5.4 Friedländer Hetero-Annulation for the Synthesis of Quinoline Derivatives
5.5 Synthesis of Furan, Pyrrole, and Thiophene Derivatives
5.6 Synthesis of Benzimidazole Derivatives
6 Reactions of Sugars
6.1 Stereoselective Synthesis of C-Pseudoglycals
6.2 Condensation of delta-Hydroxy-a,beta-Unsaturated Aldehydes with an Aryl Amine
7 Deprotection Reactions
7.1 Cleavage of Alkyl tert-Butyl Trimethylsilyl Ether
7.2 Cleavage of Trityl Ethers
7.3 Cleavage of Acetals
8 Reactions of Quinones
8.1 Allylation of Quinones
8.2 Acylation of p-Quinone
9 Conclusion
References
Index

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